My Favourite Things: Chelsea Boots


For a man who acknowledges that his own shoe collection has always been excessive – and in truth, is now simply out of control – my collection of boots is surprisingly modest; one pair of black, and one pair of tan Chelsea boots. Generally speaking, boots, though comforting, cosy-looking and deliciously toasty, have never really appealed to me. Aside from a few rare (and generally very expensive) examples, the lace-up styles are not particularly graceful; clumpy and commando soled, they are only really suitable for trekking or après-ski. Unless you are Orlando Bloom, they will look absurd in a metropolitan context.

Chelsea boots are an altogether different thing. Not only do they have the boot-advantage of keeping foot and ankle warm, they also have a distinctively elegant style which is as passable with midweek suits as it is with weekend casual. Purists might scoff at the use of boots with a turned-up worsted trouser but boots have a greater connection with formal attire than any other shoe – it wasn’t until the 20th century that the shoe replaced the boot in this regard. The Chelsea boot retains the toe-shape of such a boot but replaces the buttoned side-fastening with elastic. A good pair of Chelsea boots will have a narrow enough shaft to wear with a slimmish pair of suit trousers.

Their versatility and warmth are not the only reasons to invest; they are also very easy to maintain and generally excellent value for money. For the quality and quantity of leather you are purchasing, Chelsea boots – requiring less bench-work than a pair of shoes – are reasonably priced. The elastic siding also makes them comfortable to wear and easy to remove. The real question is not why you should buy a pair of Chelseas but why you shouldn’t. As Hardy Amies said “Elastic-sided boots are more comfortable to wear, easier to put on, nicer to look at, and better integrated with the rest of one’s clothes than the lace-up kind. They seem to have just about everything in their favour.”

Because of the beautifully uninterrupted expanse of the leather, brown burnished boots are particularly attractive. The leather takes on a glorious depth; from light tan notes to deep chestnut. Though black boots are more popular and more practical for midweek wear my weekend browns, lightly burnished from years of use and polishing, are without a doubt one of my greatest winter comforts.

Where Do They Get Their Ideas From?

I imagine anybody who has designs on producing clothes will at some point suffer niggling doubts. The one that gets me from time is can I keep coming up with new ideas?

They say there’s no such thing as an original idea. That’s not strictly true of course. There is originality in high fashion, but sending men down the catwalk in sequin caftans, Bermuda shorts and hobnail boots is of no interest to me.

But even classically minded producers of clothes must come up with new products and designs at least twice a year. So, where do the designers get their ideas?


In fact they do the same thing that I’ve been doing. I’ve amassed old black and white photos from flea markets, magazine clippings; a huge file of images taken from websites like the Sartorialist; collections of old movies and a trawl of London’s excellent vintage shops. This last source is in fact the most logical path and one most heavily tramped.

You may already know that Jeremy Hackett’s first retail endeavour was a vintage shop on the King’s Road. What’s less well known is that a regular customer was Ralph Lauren. Once Hackett began remaking items that took his fancy from within his vintage stock the label we know today was born.

He is far from the only one, and London is well served for archives of vintage clothing and apparel. To begin with there is Portobello Road market. Held every Saturday it’s the largest open air antiques market in the World. It hosts a multitude of vintage clothes and military apparel stalls, as well as kit from new upcoming designers. The likes of Paul Smith and Ozwald Boateng are reputed to stalk the stalls, seeking inspiration for everything from buttons to tweed blazers.

Other favourites include Old Hat – whom we highlighted here.


My favourite vintage shop, Emporium, is where I picked up my denim jacket. Although not specialising in one particular area they’re a good place to start if you’re looking for a 60s or Mod vibe. Jonathan has a huge private collection which designers can view by appointment. Not only does he help a number of well known designers, he and his wife also undertake work with film and television wardrobe departments.


A relative newcomer is The Vintage Showroom. They specialise in 40s and 50s British military apparel and American orientated work wear. They’ve collaborated with both Garbstore and North Sea Clothing in the past. As well as the retail unit they have a large collection available to view by appointment. Their website gives a flavour of what they offer.


Next door to The Vintage Showroom is MINT. I’d say the styling was more 50’s. Here you’ll find rows of vintage washed denim and plaid shirts.

While you may never visit these shops, it’s a reasonable bet the folks who design your clothes have.

The Way You Wear Your Hat: The Top Hat


Ideally, all advice should be seasonal. The weather report is the perfect example of why words of wisdom have a time as well as a place; no one wants to know how sunny it’s going to be in June in the dark hours of December. I have always considered that the fashion world is in a constantly unreal and very disagreeable state; reviewing summer clothing in winter, writing about furs in the heat of June. Awful. Sartorial advice should preferably cling to the relevant issues of the season, otherwise like all unseasonal advice – like that of a mother warning against the fripperies of collegiate distractions at the beginning of summer instead of the first weeks of autumn – it gets ignored.

However, I have long considered that style is about more than clothes and I have been aching to write a new series not on clothing itself but the manner in which it is, and the manner in which it could be, worn. Once a gentleman has settled on a houndstooth jacket or a polka dot tie he has only completed half of the required steps towards presenting himself in the best possible way; to avoid dispensing opinion on the last few steps is to miss an opportunity. It would be a disservice; no one wants to have a wheel half-fitted.

For the series, I have humbly borrowed Ira Gershwin’s line from one of the more famous numbers from the Astaire feature Shall We Dance. Appropriately, but perhaps slightly out of season, we begin with a feature on hats, and not just any hat but the king of hats; the topper. Hopelessly out of fashion and consistently declining in use, the still-wonderful top hat is required wear at Royal Ascot in the warmer months and is also optional for morning dress at weddings. Aside from a tiny number of period-clothing devotee dandies, this is as much use as it gets this side of the pond; even the royals only wear it when they have to. I have no idea whether it is required in the United States, or even expected; so antiquated is it as an item of headgear I would not be surprised if the only top hats stateside are the ones spotlit in museums.

However, it is often a popular choice for fancy dress and indeed for fancy dressers. It has followers and collectors, like any iconic item of clothing, and however small the interested audience, the top hat is still known today; few people of any class are unfamiliar with the design. Perhaps due to its rarity, when the time comes for use, some are confused as to how it should fit and how it should be worn. Firstly, I would advise anyone interested in owning their own topper to get their hands on an antique silk version. The modern felt versions are not inexpensive and their simulation of silk, while not exactly dreadful, isn’t even close to the deep shine possible with the original.

At good milliners like Locks, antique silk top hats are prohibitively priced. The quality may be high but the cost is eye watering. The real bargains are to be found on eBay where a silk topper of reasonable quality may be purchased for less than £100 – relatively far less than a gentleman would have paid in 1890.

Once a good silk hat of the appropriate size has been secured, it will need consideration before use. Firstly, the top hat should sit snugly on a gentleman’s head; a loose top hat is a liability. One does not want to induce a headache but a little padding in the inside band may be required to achieve the correct fit. Secondly, this fit should achieve a placement on the top of a gentleman’s head – it should sit high and proud, not be allowed to sink to the top of his ears. From the image above, you can see that the gentlemen visitors to Ascot at top-left have allowed this to happen; their hats appear wide and ill-fitting, as they falls to their ears. The antiquated images of Ascot-goers and others display how different, and in my opinion more elegant, the hat looks when it sits on the top of the head, allowing clear space between the top of the ears and the bottom of the hat, as well as the subtle angle of wear. Always remember: the ‘top’ hat is for the ‘top’ of the head.

In Search Of Good Tailoring


Michael Anton (writing under the pseudonym Nicholas Antongiavanni) wrote in The Suit: A Machiavellian Approach to Men’s Style that “since tailored clothing can make a man look either rakish or ridiculous, as well as shorter or taller or fatter or thinner, it is necessary for him to choose models, fabrics, and patterns that flatter his shape while minimizing its defects.” While the man of average height and weight can wear most anything off-the-rack and achieve a flattering result, I find that most ready-to-wear clothing is unflattering on me. I have short legs that are out of proportion to my long torso, some slight middle-age spread and a protruding posterior. Most of the ready-to-wear suits on the market in the United States combine a single-breasted, center-vented jacket with pleated, low waisted trousers. Low-waisted trousers sit under my belly and visually chop me off at the waist, accentuating both my short legs and extra weight. My protruding rear wreaks havoc with center vents. I have come to the inescapable conclusion that to achieve the look I desire will require bespoke clothing.

I made my first foray into custom-made clothing earlier this summer when I ordered a made-to-measure navy double-breasted hopsack blazer from Tom James. That jacket arrived with some serious fit issues that were (after cutting two new sleeves) eventually mostly sorted out. One sleeve is still a little longer than the other and the button placement is a little off, but both of those issues can probably be fixed before I put it back into the rotation next spring. Nevertheless, I have received numerous compliments on the blazer and think that it turned out reasonably well.

From my experience with the Tom James blazer, I came to understand the value of fittings during the  construction of tailored clothing, and the problems that can arise without such fittings. At a basted fitting a tailor will have sewn the basic parts of the suit together with white cotton basting thread. This fitting gives the tailor the chance to correct any major errors in your pattern. At the forward fitting the suit will be nearly complete. This fitting gives the tailor a final chance to correct any minor details before the suit is completed. Even after the suit is complete, minor tweaks may be necessary.

Armed with a desire for a custom suit and my previous dubious experience with MTM clothing, I made a road trip to Atlanta, GA, this past weekend to meet with a traveling tailor from Hemrajani Tailors. When I arrived in his hotel suite I saw an array of fabric books laid out on a large table.  We discussed the type of suit I was interested in having made and began to look at some fabric swatches. While we looked at the fabrics I inquired about the basted fitting. My assumption was that I would have to make another trip in several months to catch up with him on his travel route for the basted fitting. I was then informed that there would be no fittings; a completed suit based on measurements taken that day would be shipped to my door in six to eight weeks. I dropped back to punt.

The trip was not a complete waste.  I have for some time wanted to order an unlined shirt jacket like the ones often worn by the late French actor Philippe Noiret.  Those of you that read Will Boehlke’s blog A Suitable Wardrobe may have seen the linen and wool versions that he has written about in the past. I placed an order for a shirt jacket in the pictured brown tweed. It will have four bellows pockets, coordinating bone buttons, and a small slit at the bottom  of each side for easy access to trouser pockets. Mr. Boehlke’s shirt jackets are made by Hemrajani Tailors so I was comfortable placing a MTM order for that item. I will write a follow-up about the shirt jacket when it arrives in the next couple of months.

In the meantime, I am still in search of a tailor. Access to quality tailoring is a real challenge while living in a small town in the American South. Sometimes I envy those of you living in New York or London. Oh well, we have better BBQ.  On a serious note, if anyone has a recommendation for a good tailor in cities like Charleston or Atlanta, or knows of one that travels through the American South, please post a comment. I’d like to check them out.

The Question Of Trying


One of the most fascinating accusations levelled at me is that, in my manner of dress, I try far too hard. This has always been a sore point for me but not, as you might expect, because I experience personal wounding from the insult. Rather it is frustratingly perplexing to me that commentators can deliver in the manner of a fait accompli such dissatisfaction with, not a result, but the appearance of effort in attaining that result. Additionally, the pretence of such commentators with regards to their acquaintance with the intimacies of my mental and physical exertions when we do not even maintain the slightest sense of a communicative relationship is absolutely staggering. An aesthetic criticism seems legitimate to me; “Too fussy”, “Too derivative”, “Too bright” – these are opinions based on evidence. “You’re trying WAY too hard” on the other hand is not based on evidence but is simply a speculation.

Firstly, the concept of trying is a relative one. People who are aesthetically inclined and colour-minded may naturally find it easier to throw a few items together and make an outfit. In much the same way that a skilled composer can produce an original and beautiful tune in a matter of minutes, or an artist produce a compelling portrait in under an hour; the result is not always a sign of considerable time-investment. Secondly, it should not be that a sign of trying, phantom or otherwise, is so repugnant to the man in the street. Effort is denigrated too often and too wantonly and has become a dirty word in an increasingly laid-back, barely sentient, dozy excuse for a developed world. Trying is apparently wrong and trying too hard a mortal sin.

My participation in a recent Esquire competition to find Britain’s Best Dressed Real Man exposed me to the opinion of a vast array of forum-trawlers, many of whom exhibited sheer indignation and contempt for any entry that appeared to involve ‘trying.’ What was most interesting was that the most complimentary and the most critical rounded on the same issue; “…You can see what he is trying to do here” vs. “…he is trying waaaaaaay too hard.” Again, the appearance of trying (however disingenuous that effect might be) the subject of chief concern; not colour, not pattern, not the mixture of fabrics.

A friend informed me that any number of entries in the competition would receive such critiques because individuals do not consider themselves ‘qualified’ enough to analyse compositions for their result because they cannot compute the personal effort required on their behalf to simulate the same effect.

This is perhaps rather harsh, and as speculative a charge as that of someone telling me I try too hard, but it does touch upon a deeper sociological topic: ‘trying’, in relation to creativity, is the easiest thing to stigmatise as the results of an aesthetic pursuit are always subjective. It also attacks the integrity of the creator to mark a result as one of industry rather than inspiration. Unless such bitterness is expunged, I expect in ten years or so a gentleman wearing anything more involved than a GAP fleece and a pair of training shoes to be scorned as an, ahem, ‘trying’ individual.